ethyl 5-cyanobiphenyl-2-carboxylate | 1209469-79-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 5-cyanobiphenyl-2-carboxylate
• CAS: 1209469-79-3
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: IMMDPFFQENEEEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.09
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-氰基苯甲酸乙酯 、 碘苯 在 TMP₂Zn*2MgCl₂*LiCl 、 三(2-呋喃基)膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 53.0h， 以84%的产率得到ethyl 5-cyanobiphenyl-2-carboxylate
  参考文献：
  名称：

  Scaleable Preparation of Functionalized Organometallics via Directed Ortho Metalation Using Mg- and Zn-Amide Bases

  摘要：

  A range of aryl and heteroaryl organometallics are efficiently prepared in THF via directed ortho metalation by using the previously reported amide bases tmpMgCl center dot LiCl (tmp = 2,2,6,6-tetramethylpiperidyl), tmp(2)Mg center dot 2LiCl and tmp(2)Zn center dot 2MgCl(2)center dot 2LiCl. These metalation reactions are carried out at 80-100 mmol scale. The unsaturated organometallic compounds undergo smooth reactions with various electrophiles, e.g. additions to carbonyl groups, Pd-catalyzed cross-coupling reactions or Cu-catalyzed acylations. In all cases, the metalation rates have been compared with corresponding small-scale reactions (1-2 mmol). Moreover, a procedure for the recovery of the valuable tmp-H from the aqueous layer is reported.

  DOI：

  10.1021/op9002888